From e39dc7976cd8d032c4d44a22b1a5ed275d88b4c5 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?T=C3=82CHES?= <afromanguy@me.com>
Date: Tue, 24 Mar 2026 22:26:39 -0600
Subject: [PATCH] fix(gsd): insert DB row when generating milestone ID (#2416)

gsd_milestone_generate_id creates a minimal DB row (status: 'queued')
via INSERT OR IGNORE when generating an ID. This ensures milestones
created via /gsd queue or multi-milestone discuss are visible to the
state machine from the moment they get an ID, rather than relying on
the safety-net reconciliation in deriveStateFromDb().

Co-authored-by: Claude Opus 4.6 (1M context) <noreply@anthropic.com>
---
 .../extensions/gsd/bootstrap/db-tools.ts      | 19 +++++++++++++
 .../gsd/tests/derive-state-db.test.ts         | 27 +++++++++++++++++++
 2 files changed, 46 insertions(+)

diff --git a/src/resources/extensions/gsd/bootstrap/db-tools.ts b/src/resources/extensions/gsd/bootstrap/db-tools.ts
index 759bfe256..70edc4e30 100644
--- a/src/resources/extensions/gsd/bootstrap/db-tools.ts
+++ b/src/resources/extensions/gsd/bootstrap/db-tools.ts
@@ -248,6 +248,7 @@ export function registerDbTools(pi: ExtensionAPI): void {
       // This guarantees the ID shown in the UI matches the one materialised on disk.
       const reserved = claimReservedId();
       if (reserved) {
+        await ensureMilestoneDbRow(reserved);
         return {
           content: [{ type: "text" as const, text: reserved }],
           details: { operation: "generate_milestone_id", id: reserved, source: "reserved" } as any,
@@ -259,6 +260,7 @@ export function registerDbTools(pi: ExtensionAPI): void {
       const uniqueEnabled = !!loadEffectiveGSDPreferences()?.preferences?.unique_milestone_ids;
       const allIds = [...new Set([...existingIds, ...getReservedMilestoneIds()])];
       const newId = nextMilestoneId(allIds, uniqueEnabled);
+      await ensureMilestoneDbRow(newId);
       return {
         content: [{ type: "text" as const, text: newId }],
         details: { operation: "generate_milestone_id", id: newId, existingCount: existingIds.length, uniqueEnabled } as any,
@@ -272,6 +274,23 @@ export function registerDbTools(pi: ExtensionAPI): void {
     }
   };
 
+  /**
+   * Insert a minimal DB row for a milestone ID so it's visible to the state
+   * machine. Uses INSERT OR IGNORE — safe to call even if gsd_plan_milestone
+   * later writes the full row. Silently skips if the DB isn't available yet
+   * (pre-migration).
+   */
+  async function ensureMilestoneDbRow(milestoneId: string): Promise<void> {
+    const dbAvailable = await ensureDbOpen();
+    if (!dbAvailable) return;
+    try {
+      const { insertMilestone } = await import("../gsd-db.js");
+      insertMilestone({ id: milestoneId, status: "queued" });
+    } catch {
+      // Non-fatal — the safety-net in deriveStateFromDb will catch this
+    }
+  }
+
   const milestoneGenerateIdTool = {
     name: "gsd_milestone_generate_id",
     label: "Generate Milestone ID",
diff --git a/src/resources/extensions/gsd/tests/derive-state-db.test.ts b/src/resources/extensions/gsd/tests/derive-state-db.test.ts
index 2b8d304fb..307a51c29 100644
--- a/src/resources/extensions/gsd/tests/derive-state-db.test.ts
+++ b/src/resources/extensions/gsd/tests/derive-state-db.test.ts
@@ -11,6 +11,7 @@ import {
   insertArtifact,
   isDbAvailable,
   insertMilestone,
+  getAllMilestones,
   insertSlice,
   insertTask,
 } from '../gsd-db.ts';
@@ -995,4 +996,30 @@ describe('derive-state-db', async () => {
       cleanup(base);
     }
   });
+
+  // ─── Queued milestone row not clobbered by later plan (#2416 root cause) ──
+  test('derive-state-db: queued milestone row survives gsd_plan_milestone INSERT OR IGNORE', async () => {
+    try {
+      openDatabase(':memory:');
+
+      // Simulates gsd_milestone_generate_id inserting a minimal queued row
+      insertMilestone({ id: 'M001', status: 'queued' });
+
+      const before = getAllMilestones();
+      assert.equal(before.length, 1, 'queued-row: one row after generate_id');
+      assert.equal(before[0]!.status, 'queued', 'queued-row: status is queued');
+
+      // Simulates gsd_plan_milestone calling insertMilestone (INSERT OR IGNORE)
+      insertMilestone({ id: 'M001', title: 'Planned Title', status: 'active' });
+
+      const after = getAllMilestones();
+      assert.equal(after.length, 1, 'queued-row: still one row after plan');
+      // INSERT OR IGNORE keeps the original row — status stays 'queued'
+      assert.equal(after[0]!.status, 'queued', 'queued-row: INSERT OR IGNORE preserves original status');
+
+      closeDatabase();
+    } finally {
+      closeDatabase();
+    }
+  });
 });